Anguilla, Long Weekend

Thirty-three beaches, no cruise ships, no casinos, and not much to do. Which is entirely the point.

days: 4
bases: 3
places to eat: 4
budget: elevated

Anguilla is flat, dry, sixteen miles long, and has some of the finest sand in the Caribbean. There is no cruise pier, no casino, no significant sightseeing and no nightlife beyond a handful of beach bars. What there is: thirty-odd beaches, a restaurant scene far beyond the island's size, and a long weekend that will restore you.

What you get

The whole trip, decided.

Not a list of sights. A route someone has already walked, with the bookings that need doing early flagged, the transfers timed, and the costs written as real ranges instead of a fantasy number.

4 days: written out morning, afternoon and evening
3 bases: where to sleep each night, and why there
4 places to eat: with what to order and which base it is near
4 local tips: the things a guidebook does not tell you
A route map: showing how the whole trip fits together
Full costs: stay, food, activities and transport, broken out
6 pre-trip checks: what to confirm yourself before you book
A printable PDF: works offline, yours to keep

Why this one

Worth the flight.

Shoal Bay East, regularly ranked among the best beaches in the world
A boat to Sandy Island, a sandbar with a few palms, a grill and nothing else
Sunset at Sandy Ground, where the fishing boats and the beach bars are
Some of the best restaurants in the Caribbean, in improbably small buildings
Doing nothing at all, without apology

Best months are December, January, February, March, April, May. Expect around $1,800–4,500 per person, excluding flights for the whole 4 days, excluding flights. The guide breaks that into stay, food, activities and transport so you can see where it goes.

How this stays honest

Checked August 2026

Prices, opening days and entry rules drift, and no written guide can outrun that. So costs are always ranges rather than quotes, every plan carries the date it was last checked, and the last page is six things to confirm yourself before you book anything.

I take no commission from any hotel or operator. You book everything yourself, in your own name, at the price you can see.

See the other guides